US4089700A - Process for the preparation of opaque organic pigments - Google Patents

Process for the preparation of opaque organic pigments Download PDF

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Publication number
US4089700A
US4089700A US05/684,649 US68464976A US4089700A US 4089700 A US4089700 A US 4089700A US 68464976 A US68464976 A US 68464976A US 4089700 A US4089700 A US 4089700A
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US
United States
Prior art keywords
pigment
azeotropic
binders
forming agent
press cake
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US05/684,649
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English (en)
Inventor
Horst Brandt
Reinhold Hornle
Karlheinz Wolf
Hans-Heinz Molls
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Bayer AG
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Bayer AG
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Filing date
Publication date
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Publication of US4089700A publication Critical patent/US4089700A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0004—Coated particulate pigments or dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/0001—Post-treatment of organic pigments or dyes
    • C09B67/0003—Drying, e.g. sprax drying; Sublimation of the solvent

Definitions

  • Organic pigments such as copper phthalocyanine, quinacridones, dioxanes and, in particular, azo pigments, are obtained, after preparation and conditioning, in so far as conditioning is required, mainly in a form in which they provide transparent colour impressions in binders. If their pigment concentrations are increased in order to obtain full shade colorations, the binders to which the pigments are added exhibit flow properties which are impaired to an undesirable degree.
  • German Auslegeschrift (German Published Specification) 2,302,509 describes a process in which a pigment obtained after coupling is thoroughly stirred with alkali, filtered off, washed until neutral, optionally dried, and heated with an organic solvent, which is immiscible with water or which is not miscible with water in all proportions, to temperatures above 100° C, the organic solvent is distilled off with steam and the pigment is filtered out of the residual aqueous suspension and dried.
  • a further process in which the abovementioned processing steps are also employed, with the exception of the thorough stirring with alkali, is known from German Auslegeschrift (German Published Specification) 2,302,482.
  • the process according to the invention is characterised in that an azeotrope-forming agent appropriate for the liquid adhering to the pigment or the liquid contained in the pigment press cake is added to the moist pigment obtained after preparation, preferably to the moist pigment press cake obtained by filtration after preparation, and the azeotropic mixture and any excess solvent (azeotrope-forming agent) which may be present are then distilled off.
  • German Auslegeschrift (German Published Specification) 1,266,721 describes a process in which a dispersion of the pigment in an organic solvent is prepared by azeotropic distillation from an aqueous pigment press cake, the solvent taking up impurities from the pigment, so that the quality of the pigment is improved, and finally being separated, together with the dissolved impurities, from the pigment, by filtration.
  • German Auslegeschrift (German Published Specification) 1,115,711 describes a process in which a water-containing paste of perylene-tetracarboxylic acid diimide, which exhibits no pigment properties whatsoever, is converted into a pigment form by treatment with organic solvents.
  • Organic pigments of the azo, anthraquinone, azaporphine, thioindigo or polycyclic series as well as the quinacridone, dioxazine, naphthalenetetracarboxylic acid or perylenetetracarboxylic acid series and also copper phthalocyanines can be used as pigments which provide a transparent colour impression in binders.
  • a large number of individual pigments of these categories of substances are known, for example from Colour Index, 2nd edition.
  • the solvents which are to be distilled off as an azeotrope by means of the process according to the invention, are determined by the processes for the preparation and conditioning of the particular pigment and are known to those skilled in the art.
  • Azeotrope-forming agents suitable for these solvents are known, for example from Handbook of Chemistry and Physics, 52, 1971 to 1972. Examples of azeotrope-forming agents which may be mentioned are benzene, toluene, xylenes, butanols, propionitrile, hexan-4-one, butyl acetate and 1-butoxy-2-propanol, and these are used preferentially.
  • the process according to the invention is used for azo pigments, if these are obtained as aqueous press cakes.
  • azeotrope-forming agents which have a boiling point of preferably below 100° C and an azeotropic point with water of below 100° C are used.
  • the process is appropriately carried out that the 10 to 60 percent strength by weight, preferably 15 to 30 percent strength by weight, pigment press cake is mixed with the azeotrope-forming agent in a weight ratio 1 to (0.8 to 10) in a suitable unit and the azeotropic mixture, and, if appropriate, the excess solvent, are then distilled off.
  • suitable units are, for example, paddle driers, thin layer contact driers or similar equipment.
  • the individual process steps or the entire process can be carried out under normal pressure or in vacuo.
  • the azeotrope-forming agent can be recovered from the distillate by customary processes and recycled for renewed use.
  • the dry pigment powders obtained by the process according to the invention give opaque colorations and improved fastness to light compared with that of the transparent pigments, and display good flow properties in binders, in concentrations which give full shade colorations. Losses in depth of colour were not observed.
  • the pigments prepared in this way are used in lacquers, printing inks and plastics, in particular in conjunction with inorganic pigments.
  • the excess propionitrile is then stripped off, initially at a somewhat higher temperature and then in vacuo, until the pigment is dry.
  • the pigment displays increased covering power for an equal depth of colour and improved fastness to light and gloss formation.
  • a thin layer evaporator In place of a thin layer evaporator it is also possible to use a paddle drier, a thin layer contact drier or the like.
  • the pigment displays increased covering power for an equal depth of colour and a substantially improved fastness to light and gloss formation.
  • the flow properties of the corresponding full shade lacquers are also improved.
  • the excess propionitrile is then stripped off, initially at a somewhat higher temperature and then in vacuo, until the pigment is dry.
  • the pigment displays substantially increased covering power for about equal depth of colour as well as improved fastness to light and gloss formation.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Pigments, Carbon Blacks, Or Wood Stains (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Paints Or Removers (AREA)
US05/684,649 1975-05-13 1976-05-10 Process for the preparation of opaque organic pigments Expired - Lifetime US4089700A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DT2521249 1975-05-13
DE2521249A DE2521249C2 (de) 1975-05-13 1975-05-13 Verfahren zur Herstellung deckender organischer Pigmente

Publications (1)

Publication Number Publication Date
US4089700A true US4089700A (en) 1978-05-16

Family

ID=5946430

Family Applications (1)

Application Number Title Priority Date Filing Date
US05/684,649 Expired - Lifetime US4089700A (en) 1975-05-13 1976-05-10 Process for the preparation of opaque organic pigments

Country Status (10)

Country Link
US (1) US4089700A (enrdf_load_stackoverflow)
JP (1) JPS5833896B2 (enrdf_load_stackoverflow)
BR (1) BR7602983A (enrdf_load_stackoverflow)
CH (1) CH616449A5 (enrdf_load_stackoverflow)
DE (1) DE2521249C2 (enrdf_load_stackoverflow)
DK (1) DK210476A (enrdf_load_stackoverflow)
ES (1) ES447824A1 (enrdf_load_stackoverflow)
FR (1) FR2311065A1 (enrdf_load_stackoverflow)
GB (1) GB1499060A (enrdf_load_stackoverflow)
IN (1) IN144901B (enrdf_load_stackoverflow)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4944040A (en) * 1986-06-26 1990-07-31 Minnesota Mining And Manufacturing Company Light occlusive eye patch

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268144A (en) * 1940-03-28 1941-12-30 Harmon Color Works Inc Recovering pigments
US3119706A (en) * 1958-04-11 1964-01-28 Allied Chem Process for conditioning pigments
US3671281A (en) * 1970-09-16 1972-06-20 Gaf Corp Pyrazolone red pigment and process therefor

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB318937A (en) * 1928-03-09 1929-09-09 John William Croom Crawford Improvements in or relating to the preparation of pigments and the like
US2138048A (en) * 1935-03-04 1938-11-29 Harmon Color Works Inc Making dry, free-running pigment powders
DE1115711B (de) * 1956-09-29 1961-10-26 Hoechst Ag Verfahren zur UEberfuehrung von Perylen-3, 4, 9, 10-tetracarbonsaeurediimid in eine als Pigmentfarbstoff verwendbare Form
DE1155755B (de) * 1960-05-28 1963-10-17 Hoechst Ag Verfahren zur Herstellung von Azopigmenten mit verbesserter Fliessbarkeit
DE1179908B (de) * 1960-12-02 1964-10-22 Hoechst Ag Verfahren zur Herstellung von Azopigmenten mit verbesserter Fliessarbeit
CH426056A (de) * 1963-07-12 1966-12-15 Geigy Ag J R Verfahren zum Entwässern von Azopigmenten
GB1143727A (enrdf_load_stackoverflow) * 1966-09-09 1900-01-01
DE2302482C3 (de) * 1973-01-19 1984-01-05 Hoechst Ag, 6230 Frankfurt Disazopigment, Verfahren zu seiner Herstellung und seine Verwendung

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2268144A (en) * 1940-03-28 1941-12-30 Harmon Color Works Inc Recovering pigments
US3119706A (en) * 1958-04-11 1964-01-28 Allied Chem Process for conditioning pigments
US3671281A (en) * 1970-09-16 1972-06-20 Gaf Corp Pyrazolone red pigment and process therefor

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4944040A (en) * 1986-06-26 1990-07-31 Minnesota Mining And Manufacturing Company Light occlusive eye patch

Also Published As

Publication number Publication date
FR2311065A1 (fr) 1976-12-10
CH616449A5 (enrdf_load_stackoverflow) 1980-03-31
IN144901B (enrdf_load_stackoverflow) 1978-07-22
JPS51139827A (en) 1976-12-02
BR7602983A (pt) 1977-06-07
DE2521249C2 (de) 1983-11-10
DK210476A (da) 1976-11-14
ES447824A1 (es) 1977-07-16
JPS5833896B2 (ja) 1983-07-22
DE2521249A1 (de) 1976-12-02
GB1499060A (en) 1978-01-25
FR2311065B1 (enrdf_load_stackoverflow) 1980-08-08

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